After spending one night in Port Washington and venturing into shore the next morning, we decided we needed to keep moving. Temperatures were supposed to be in the 90’s that weekend with little wind. After consulting with our friends Jay and Tanya, aboard SV Minx, we decided to head to the opposite end of Long Island Sound to Sag Harbor, NY, where the temperatures were a bit milder.

Sag Harbor, NY

Sag Harbor was at least 5 degrees cooler, which is a lot when temps are reaching the 90’s. It definitely made things a bit more comfortable although we would have like to take our time stopping along the way throughout Long Island Sound. We decided the sightseeing here would have to wait until our return trip south.

Sag Harbor was fun, but expensive. We didn’t know much about this town until speaking with my sister and she informed us that Justin Timberlake got pulled over there forDUI just a few weeks before. Turns out, this is where a lot of wealthy New Yorkers and celebrities like to vacation. The price of laundry, provisions, etc. certainly reflected it. Also, the amount of mega yachts in the marinas and moored in the harbor were astounding. We did get to enjoy a couple of beers at a local brewery called Kidd Squid and grabbed tacos at El Taco Bar. After we blew the budget on Sag Harbor, it was time to move on.

From there, we moved a few miles north to an anchorage near Shelter Island where we stayed a couple days with our friend on SV Minx, before heading further north to anchor at Fishers Island. Once we made it Fishers Island, we stayed a couple nights until we had a weather window to make it across Block Island Sound to Cuttyhunk.

Cuttyhunk, MA

Cuttyhunk is a small island located between Buzzards Bay to the north and Vineyard Sound to the south. I would call it “quaint” and “picturesque,” but that is an understatement. With rolling hills and flowers blooming everywhere, it was simply gorgeous. Apparently, it’s home to about 10 year-round residents and in the summer, population goes into the 100’s. There isn’t a whole lot to Cuttyhunk other than panoramic views and beach going. Only a few restaurants, an ice cream shop and maybe a souvenir shop or two are there. Folks go there to relax and get away from things. We we told to be sure to climb the hills to top to get a view and it was stunning. There are several trails that take you throughout the island that it can be hilly and sandy, but worth it. We were definitely glad we made it a point to stop here.

Mattapoisett, MA

We left Cuttyhunk and had a wonderful sail across Buzzards Bay to Mattapoisett, MA. The only reason we chose to visit Mattapoisett was because we have cruising friends who have a mooring there and weren’t using it so they graciously let us use it for the summer. We knew we needed to get some big boat projects done over the summer in order to list Blue Turtle for sail, so we decided to call Mattapoisett home for a few weeks.

Mattapoisett is a very small town located on Buzzards Bay. It’s history is in whaling, alongside the town of New Bedford. The actual main road in town has only a handful of small businesses. The harbor is large with many mooring balls. One thing we noted immediately is that many of the mooring balls were occupied with small wooden sailboats, ski boats and center console boats. These moorings are mostly owned by locals and they use them as a place to keep their boats until they can use them (mostly weekends). We’re so used to seeing transient moorings where they are occupied by larger vessels like ours with people actually on them. Summer season up here is short, and with the lack of a canal system for waterfront homes, people put their boats in at the beginning of season and leave them moored so they can hop on them whenever they’re free in the summer.

Our first weekend in Mattapoisett, they held their annual Harbor Days festival which featured over 100 tents of local craftsmen and women. It was a great small-town fair to get acquainted with the town. We also quickly discovered the Mattapoisett Rail Trail and Phoenix Bike Trail that connected to each other forming 6.5 miles of wide bike and running/walking paths through both Mattapoisett and neighboring Fairhaven. We went for walks and runs with Sophie any chance we had and realized that we could also use the trail to get to the grocery and other errands we needed to run without having to travel the main roads. Both trails are very well kept and very scenic taking you across marshes and through the forest areas.

While we were able to get some boat projects done, at times, it was difficult. We realized that the harbor was not protected from a northeast wind which meant anytime the wind was out of that direction, we would have swell and waves from the fetch across the bay. This made it difficult for Randy to work on the exterior wood since many times, he would have to stand in the dingy in order to sand the lower rails. It also made it uncomfortable at times to sleep and just do anything at all. A couple of times, we just decided to go to shore and walked the trails since we didn’t want to be on the boat while the water was lumpy. One weekend, we knew the wind and waves would be relentless so we pulled anchor and headed across the bay to Hadley Harbor where it was protected from the wind.

Hadley Harbor, MA

Located at the northern tip of Naushon Island in Massachusetts, near the entrance to Woods Hole in Buzzards Bay, lies Hadley Harbor. The inner harbor is small and surrounded by private homes on the islands. There is no shore access except for on Bull Island. Free moorings are available on a first come, first served basis and we were lucky to snag one since the harbor is usually quite crowed in the summer months. We spent a couple nights on the mooring, realizing it was a bit to snug for our liking but with the winds howling, it was certainly protected, and for that we were thankful. On our third day there, we dropped the mooring and decided to anchor in the outer harbor area so Randy could get some sanding done without bothering anyone nearby. By noon that day, we pulled anchor and decided to sail back across the bay to Mattapoisett where we spent another week on the mooring there.

New Bedford, MA

Once Randy finally had the sanding done and the the exterior wood prepped, decided to book a slip in a marina so he could easily apply the Cetol. We had a list of boat projects needing attention and had really gotten nowhere in the previous weeks staying in Mattapoisett. With wind and weather determining everything for us, we were running out of summer time. We decided to stay at Pope’s Island Marina in New Bedford. This was an excellent spot for us to get things done since the harbor is protected by a hurricane wall. Even with high winds, we barely felt anything, especially since a very large yacht on the face dock was blocking us.

New Bedford is a cool little town with a history in whaling. Herman Melville shipped out from New Bedford inspiring him to write the book Moby Dick. New Bedford is known as America’s #1 fishing port which is apparent as soon as you enter the harbor and see the hundreds of ships lining the shorelines. We loved the cobblestone roads and old buildings. There were many whale themed pubs and restaurants, including Moby Dick Brewery which we visited a couple times while there. We found an amazing 80’s style arcade/restaurant/bar called Play Arcade and enjoyed live music on the roof garden and beers and vegan food from their menu.

We also enjoyed walking and running the rail trails, this time from the Fairhaven side (Phoenix Bike trail) and visited Fort Phoenix and the park there. We also visited the New Bedford Whaling Museum one morning and learned about the history, science and culture of whaling through the years.

Over the course of 3 weeks, we knocked projects off the list one by one while enjoying dock life for a change. Seems like most of the time Blue Turtle in on a dock, it’s because we are traveling home to Ft. Myers. It was nice to actually get to enjoy being on the boat while it was docked. Once we got our boat work done, we listed her for sale. This was huge weight lifted off our shoulders since it was the main thing we were focused on this summer. Now that she was listed, it was time to start enjoying summer and exploring New England!

Port Washington, NY to FlaxPond (anchorage) = 33 nm
FlaxPond (anchorage) to Sag Harbor, NY = 54 nm
Sag Harbor, NY to Coecles Bay (Shelter Island) = 4nm
Coecles Bay (Shelter Island) to Fishers Island, NY = 19 nm
Fishers Island, NY to Cuttyhunk, MA = 51 nm
Cuttyhunk, MA to Mattapoisett, MA = 16 nm
Mattapoisett, MA to Hadley Harbor, MA = 10.5 nm
 Hadley Harbor, MA to Mattapoisett, MA = 9.5 nm
Mattapoisett, MA to New Bedford, MA = 13 nm

TOTAL miles to date: = 6,856 nm